Electroluminescence device
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- BEIJING XIAHE TECHNOLOGY CO LTD
- Filing Date
- 2025-10-23
- Publication Date
- 2026-07-29
AI Technical Summary
Existing phosphorescent OLEDs face challenges such as unsaturated blue emission, short device lifetime, high operating voltage, and efficiency degradation at high brightness, particularly in blue phosphorescent devices, limiting their commercialization.
A novel electroluminescent device incorporating a specific material combination comprising a first metal complex with a ligand of structure Formula 1, a first compound of structure Formula 2 or 3, and a second compound of structure Formula 4, which are used in the light-emitting layer to enhance efficiency and extend device lifespan.
The novel material combination achieves higher efficiency, significantly improves device performance, and extends the service life of electroluminescent devices, addressing the limitations of existing phosphorescent OLEDs.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to organic electronic devices such as organic light-emitting devices, and more particularly to electroluminescent devices comprising a first metal complex including a ligand having a structure represented by Formula 1, a first compound having a structure represented by Formula 2 or Formula 3, and a second compound having a structure represented by Formula 4, and display assemblies including the electroluminescent devices. [Background technology]
[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device containing an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and emissive layers (Applied Physics Letters, 1987, 51(12):913-915). Once a bias was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may contain multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer tremendous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them highly suitable for specialized applications, such as fabrication on flexible substrates.
[0004] OLEDs are divided into three different types depending on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. Triplets generated in the device are wasted through nonradiative decay pathways, resulting in an internal quantum efficiency (IQE) of only 25%, hindering the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs, which use triplet emission from heavy metal-containing complexes as the emitter. Therefore, singlet and triplet emissions can be harvested, achieving an IQE of 100%. Due to their high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, allowing excitons to transition from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons by triplet excitons threading between reverse systems (reverse intersystem crossing).
[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material used. Small molecules refer to non-polymeric organic or organometallic materials, and as long as they have a precise structure, the molecular weight of the small molecule can be large. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Post-polymerization during the manufacturing process can turn small molecule OLEDs into polymer OLEDs.
[0006] Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of an OLED can be achieved by the structural design of the emissive material. An OLED may contain one or more emissive layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still suffer from problems such as unsaturated blue, short lifetime, and high operating voltage. Commercially available full-color OLED displays generally use a mixed strategy, employing blue fluorescence and yellow, red, or green phosphorescence. Currently, phosphorescent OLEDs suffer from a rapid decrease in efficiency at high brightness. Furthermore, there is a demand for more saturated emission spectra, higher efficiency, and longer device lifetimes.
[0008] In its previous patent application US20220109118A1, the applicant of the present invention [ka] In the literature, attention has been paid to the excellent performance of metal complexes containing ligands having such novel structures, and the performance of devices when such metal complexes are used in combination with a single host material has been disclosed, but there has been no disclosure or teaching of improved device performance when a metal complex having more fused ring structures at specific positions of the ligand is used in combination with two specific host materials.
[0009] In order to meet the ever-increasing needs in the industry for various aspects of the performance of electroluminescent devices, such as luminous efficiency and device lifespan, there is still an urgent need to study phosphorescent devices. In the study of phosphorescent devices, the combination of phosphorescent material and host material is extremely important, and the selection of the combination of phosphorescent material and host material is directly related to the luminescent performance of the device. Therefore, the selection and optimization of the combination of phosphorescent material and host material has become an important part of related studies in the industry. [Prior art documents] [Patent documents]
[0010] [Patent Document 1] U.S. Patent Application Publication No. US20220109118 [Non-patent literature]
[0011] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]
[0012] The present invention aims to provide an electroluminescent device having a novel material combination to solve at least some of the above-mentioned problems. The organic layer of the electroluminescent device includes a novel material combination consisting of a first metal complex including a ligand having a structure represented by Formula 1, a first compound having a structure represented by Formula 2 or Formula 3, and a second compound having a structure represented by Formula 4. This novel material combination can be used in the light-emitting layer of the electroluminescent device. This novel material combination can achieve higher efficiency in the device, significantly improve service life, and provide better device performance. [Means for solving the problem]
[0013] According to one embodiment of the present invention, there is provided an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprises a first metal complex, a first compound, and a second compound; The first metal complex comprises a metal M and a ligand L coordinated with M. a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a has a structure represented by formula 1, [ka] ring A, ring B, and ring C are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 30 carbon atoms, or a heteroaryl ring having 3 to 30 carbon atoms; R i , R ii , R iii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R iii , R x and R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring, The first compound has a structure represented by Formula 2 or Formula 3, [ka] [ka] W may be the same or different for each occurrence. w or N, and adjacent substituents R w may be bonded to form a ring, L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R w are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The second compound has a structure represented by formula 4: [ka] In formula 4, L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 ~Ar 43 and each occurrence of each of these may be the same or different and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof. According to another embodiment of the present invention, there is further disclosed a display assembly including an electroluminescent device as described in the above embodiment. According to another embodiment of the present invention, there is provided a compound composition comprising a first metal complex, a first compound, and a second compound, The first metal complex comprises a metal M and a ligand L coordinated with M. a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a has a structure represented by formula 1, [ka] ring A, ring B, and ring C are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 30 carbon atoms, or a heteroaryl ring having 3 to 30 carbon atoms; R i , R ii , R iii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R iii , R x and R y are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring, The first compound has a structure represented by Formula 2 or Formula 3, [ka] [ka] W may be the same or different for each occurrence.w or N, and adjacent substituents R w may be bonded to form a ring, L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R w are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The second compound has a structure represented by formula 4: [ka] In formula 4, L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 ~Ar 43 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.
[0014] The present invention discloses a novel electroluminescent device, the organic layer of which comprises a novel material combination consisting of a first metal complex containing a ligand having a structure represented by Formula 1, a first compound having a structure represented by Formula 2 or Formula 3, and a second compound having a structure represented by Formula 4, and this novel material combination can be used in the light-emitting layer of the electroluminescent device. This novel material combination can achieve higher efficiency in the device, significantly improve the service life, and provide better device performance. [Brief explanation of the drawings]
[0015] [Figure 1] 1 is a schematic diagram of an organic light emitting device that may contain an electroluminescent element according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light-emitting device that may contain an electroluminescent element according to the present invention. DETAILED DESCRIPTION OF THE INVENTION
[0016] OLEDs can be fabricated on a variety of substrates, including glass, plastic, and metal. FIG. 1 illustrates, by way of example and not limitation, an organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted from the drawings, if necessary. Device 100 may include a substrate 101, an anode 110, a hole-injection layer 120, a hole-transport layer 130, an electron-blocking layer 140, an emissive layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. Device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.
[0017] There are many examples of each of these layers. Illustratively, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., incorporated herein by reference in its entirety. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin metal layer, such as Mg:Ag, coated thereon with a sputter-deposited transparent conductive ITO layer. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties, describe the principles and use of blocking layers in more detail. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, provides examples of injection layers. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, describes protective layers.
[0018] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.
[0019] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
[0020] An OLED also requires an encapsulation layer. As shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 to protect against harmful substances, such as moisture and oxygen, from the outside. Any material capable of providing an encapsulation function, such as glass or an organic-inorganic hybrid layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the exterior of the OLED device. Multilayer thin-film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.
[0021] Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lamps, head-up displays, fully or partially transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and tail lights.
[0022] The materials and structures described herein may also be used in the other organic electronic devices listed above.
[0023] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is relatively far from the substrate. Other layers may be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if various organic layers are present between the cathode and anode.
[0024] "Solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0025] It is believed that if a ligand directly enhances the photosensitizing properties of the emitting material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emitting material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand can modify the properties of the photosensitizing ligand.
[0026] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistics limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0027] On the other hand, E-type delayed fluorescence relies on the conversion of triplet and singlet excited states rather than the collision of two triplets. Compounds capable of generating E-type delayed fluorescence must have an extremely small singlet-triplet gap to allow for the energy state conversion. Thermal energy can activate the triplet-to-singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading between reverse intersystems (RISC) is sufficiently fast, the non-radiative decay from the triplet can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlets can be 100%, far exceeding the 25% spin statistics of the exciton due to electrochemical reactions.
[0028] The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T ) is required. Organic non-metal-containing donor-acceptor emissive materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, ΔE S-T These states may include CT states. Donor-acceptor emissive materials are typically constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
[0029] Definitions of Substituent Terminology
[0030] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.
[0031] As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. Illustrative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. The alkyl group may be substituted.
[0032] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may be substituted.
[0033] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropylsilylethyl. Heteroalkyl groups may also be substituted.
[0034] As used herein, the term "alkenyl group" includes linear, branched, and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornylalkenyl groups. The alkenyl groups may be substituted.
[0035] As used herein, the term "alkynyl group" includes straight-chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, and phenylpropynyl groups. Of these, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. The alkynyl group may be substituted.
[0036] As used herein, the term "aryl group" or "aromatic group" refers to both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-dimethylphenyl, mesitylene, and m-tetraphenyl. The aryl group may also be substituted.
[0037] As used herein, the term "heterocyclic group" or "heterocycle" refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. The heterocyclic group may also be substituted.
[0038] As used herein, the term "heteroaryl group" refers to both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. The term "isoaryl group" also refers to heteroaryl groups. The heteroaryl group may be a heteroaryl group containing 3 to 30 carbon atoms, preferably a heteroaryl group containing 3 to 20 carbon atoms, and more preferably a heteroaryl group containing 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Heteroaryl groups may also be substituted.
[0039] As used herein, the alkoxy group refers to an -O-alkyl group, an -O-cycloalkyl group, an -O-heteroalkyl group, or an -O-heterocyclic group. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group, and the heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may be substituted.
[0040] As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.
[0041] As used herein, the term "aralkyl group" includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.
[0042] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. The alkylsilyl group may also be substituted.
[0043] As used herein, the term "arylsilyl group" refers to a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.
[0044] As used herein, the term "alkylgermanium group" includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and is preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of the alkylgermanium group include a trimethylgermanium group, a triethylgermanium group, a methyldiethylgermanium group, an ethyldimethylgermanium group, a tripropylgermanium group, a tributylgermanium group, a triisopropylgermanium group, a methyldiisopropylgermanium group, a dimethylisopropylgermanium group, a tri-tert-butylgermanium group, a triisobutylgermanium group, a dimethyl-tert-butylgermanium group, and a methyldi-tert-butylgermanium group. The alkylgermanium group may also be substituted.
[0045] As used herein, the term "arylgermanium group" refers to a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, and preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenyldibiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. The arylgermanium group may also be substituted.
[0046] The "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the replacement of one or more C—H groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.
[0047] In the present invention, unless otherwise specified, the following groups are included: a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, When any of the terms "substituted sulfinyl group," "substituted sulfonyl group," and "substituted phosphino group" is used, it means that any one of the alkyl group, cycloalkyl group, heteroalkyl group, heterocyclyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is substituted with deuterium, halogen, non- Substituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, and unsubstituted heteroaryl groups having 3 to 30 carbon atoms. This means that the aryl group may be substituted with one or more groups selected from the group consisting of unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
[0048] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.
[0049] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.
[0050] In the compounds referred to herein, multiple substitution refers to a range up to the most available substitution, including double substitution. When a substituent in a compound referred to herein is referred to as multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on the bond structure, and the substituents present at all available substitution positions may be the same structure or different structures.
[0051] Unless specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, and adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents are not bonded to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such descriptions, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
[0052] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]
[0053] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]
[0054] The statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that two substituents bonded to carbon atoms further apart are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]
[0055] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. An example is shown in the following formula. [ka]
[0056] According to one embodiment of the present invention, there is provided an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprises a first metal complex, a first compound, and a second compound; The first metal complex comprises a metal M and a ligand L coordinated with M. a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L a has a structure represented by formula 1, [ka] ring A, ring B, and ring C are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 30 carbon atoms, or a heteroaryl ring having 3 to 30 carbon atoms; R i , R ii , R iii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R iii , R x and R y are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring, The first compound has a structure represented by Formula 2 or Formula 3, [ka] [ka] W may be the same or different for each occurrence.w or N, and adjacent substituents R w may be bonded to form a ring, L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R w are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The second compound has a structure represented by formula 4: [ka] In formula 4, L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 ~Ar 43 and each occurrence of each of these may be the same or different and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.
[0057] According to one embodiment of the present invention, R iii There is at least one R iii is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having 0 to 20 carbon atoms.
[0058] According to one embodiment of the present invention, the R iiiis the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof.
[0059] According to one embodiment of the present invention, the R iii is the same or different at each occurrence and is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.
[0060] In this specification, adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring means that adjacent substituent groups, for example, adjacent substituents R i adjacent substituents R x adjacent substituents R y adjacent substituents R ii adjacent substituents R iii adjacent substituents R i and R x adjacent substituents R i and R y adjacent substituents R i and R ii adjacent substituents R i and R iii adjacent substituents R x and R y adjacent substituents R x and R iii adjacent substituents Ry and R, adjacent substituents R y and R iii adjacent substituents R and R ii between adjacent substituents R and R iii This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of the substituents may be bonded to form a ring.
[0061] According to one embodiment of the present invention, the L a wherein ring A, ring B, and ring C are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 18 carbon atoms, or a heteroaryl ring having 3 to 18 carbon atoms.
[0062] According to one embodiment of the present invention, the L a wherein ring C is selected from an aryl ring having 6 to 18 carbon atoms or a heteroaryl ring having 6 to 18 ring atoms.
[0063] According to one embodiment of the present invention, the L a wherein ring A and / or ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 10 carbon atoms, or a heteroaryl ring having 3 to 10 carbon atoms, and ring C is selected from an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 6 to 10 ring atoms.
[0064] According to one embodiment of the present invention, the L a is selected from the structures represented by any one of formulas 1-a to 1-r, [ka] In formula 1-a to formula 1-r, X1 to X2 may be the same or different at each occurrence and may represent CR x or N, and X3 is CR i or N, and A1 to A6 are the same or different at each occurrence and are selected from CR ii or N, and X4 to X7 are the same or different for each occurrence and are selected from CR iiior N, and at least one of X4 to X7 is CR iii Selected from Z may be the same or different for each occurrence. iv R iv , SiR iv R iv , PR iv , O, S or NR iv Selected from two R iv When two R iv are the same or different, Y is SiR y R y , N.R. y , PR y , O, S or Se, and two R y When two R y are the same or different, R, R x , R y , R i , R ii , R iii and R ivare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R, R ii , R iii and R iv may be bonded to form a ring.
[0065] In this specification, adjacent substituents R i , R x , R y , R, R ii , R iii and R iv may be bonded to form a ring means that adjacent substituent groups, for example, adjacent substituents R i adjacent substituents R x adjacent substituents R y adjacent substituents R ii adjacent substituents R iii adjacent substituents R iv adjacent substituents Ri and R x adjacent substituents R i and R y adjacent substituents R i and R iii adjacent substituents R x and R y adjacent substituents R x and R iii adjacent substituents R y and R, adjacent substituents R y and R iii adjacent substituents R y and R iv adjacent substituents R and R ii adjacent substituents R and R iv each other and adjacent substituents R ii and R iv This means that any one or more of the adjacent substituents may be bonded to form a ring. Obviously, the adjacent substituents do not have to be bonded to form a ring.
[0066] According to one embodiment of the present invention, the L a is selected from the structures represented by formula 1-a or formula 1-b.
[0067] According to one embodiment of the present invention, the L a is selected from the structure represented by formula 1-b.
[0068] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 to X n and / or A1-A m At least one of the X is selected from N, n corresponds to the largest number present in any one of the formulas 1-a to 1-r of X1 to X7, and m corresponds to the largest number present in any one of formulas 1-a to 1-r of A1 to A6. For example, for formula 1-a, n corresponds to X7, which is the largest number present in formula 1-a among the X1 to X7, and mcorresponds to A4, which is the largest number of A1 to A6 present in formula 1-a, that is, in formula 1-a, at least one of X1 to X7 and / or A1 to A4 is selected from N.
[0069] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 to X n At least one of the X is selected from N, n corresponds to the largest number present in any one of formulas 1-a to 1-r of X1 to X7.
[0070] According to one embodiment of the present invention, X2 is N in formulas 1-a to 1-r.
[0071] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 and X2 are each independently CR x Selected from X3, CR i A1 to A6 are each independently selected from CR ii X4 to X7 are selected from the following, and X4 to X7 are the same or different for each occurrence. iii and adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring.
[0072] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 and X2 are each independently CR x Selected from X3, CR i A1 to A6 are each independently selected from CR ii X4 to X7 are selected from the group consisting of CH and CR, and each occurrence may be the same or different. iii and at least one of X4 to X7 is CR iii and wherein R iiiis selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 to 30 carbon atoms, selected from heteroaryl groups, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring.
[0073] In this specification, adjacent substituents R x , R i , R ii , R iii may be bonded to form a ring means that adjacent substituent groups, for example, adjacent substituents R x adjacent substituents R i adjacent substituents R ii adjacent substituents R iii adjacent substituents R i and R x adjacent substituents R x and R iii each other and adjacent substituents R i and R iiiThis means that any one or more of the substituents may be bonded to form a ring. Obviously, none of the substituents may be bonded to form a ring.
[0074] According to one embodiment of the present invention, the R x , R i , R ii are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; R iii is the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof.
[0075] According to one embodiment of the present invention, the R x , R i , R ii at least one or two of, each occurrence, are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; R iiiis the same or different at each occurrence and is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.
[0076] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, at least one or two of A1 to A4 are CR ii Selected from X3, CR i Selected from And the R i are the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof; R ii are the same or different at each occurrence and are selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.
[0077] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, at least one or two of A1 to A4 are CR ii Selected from X3, CR i Selected from And the R ieach occurrence may be the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof; R ii is the same or different at each occurrence and is selected from the group consisting of deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.
[0078] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, R is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
[0079] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, trimethylsilyl, or a combination thereof.
[0080] According to one embodiment of the present invention, Y is selected from O or S in formulas 1-a to 1-r.
[0081] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 and X2 are each independently CR x Selected from.
[0082] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 and X2 are each independently CR x wherein R x are the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
[0083] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 is CR x and X2 is N.
[0084] According to one embodiment of the present invention, in Formula 1-a to Formula 1-r, X1 is CR x X2 is N, and R x is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
[0085] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 5, [ka] In formula 5, Y is selected from O or S; R x1 , R x2 , R i , R ii1 , R ii2 , R ii3 , R ii4 , R, R iii1 , R iii2 , R iii3 , R iii4 are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, and combinations thereof; R iii1 , R iii2 , R iii3 , R iii4 and at least one of the following may be the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, and combinations thereof.
[0086] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 5, [ka] In formula 5, Y is selected from O or S; R x1 , R x2 , Riii1 , R iii2 , R iii3 , R iii4 At least one or two of the following, and / or R ii1 , R ii2 , R ii3 , R ii4 and at least one or two of R are, each occurrence, the same or different, selected from deuterium, halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; and R is selected from halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof.
[0087] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 5, [ka] In formula 5, Y is selected from O or S; R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following, and / or R ii1 , R ii2 , R ii3 , R ii4and at least one or two of R are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; and R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
[0088] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 5, [ka] In formula 5, Y is selected from O or S; R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following, and R ii1 , R ii2 , R ii3 , R ii4and at least one or two of R are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; and R is selected from halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof.
[0089] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 5, [ka] In formula 5, Y is selected from O or S; R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following, and R ii1 , R ii2 , R ii3 , R ii4and at least one or two of R are the same or different at each occurrence and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; and R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
[0090] According to one embodiment of the present invention, in Formula 5, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.
[0091] According to one embodiment of the present invention, in Formula 5, R x1 , R x2 , R iii1 , R iii2 , R iii3 , R iii4 , R ii1 , R ii2 , R ii3 , R ii4At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.
[0092] According to one embodiment of the present invention, the L a L a1 ~L a437 wherein said L a1 ~L a437 The specific structure is shown in claim 12.
[0093] According to one embodiment of the present invention, the L a L a1 ~L a438 wherein said L a1 ~L a437 The specific structure of is shown in claim 12. a438 The specific structure is as follows: [ka]
[0094] According to one embodiment of the present invention, the L a1 ~L a437 The hydrogen atoms in the structure may be partially or completely deuterated.
[0095] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b ) n (L c ) q having the structure The metal M is selected from metals with a relative atomic mass greater than 40, and L a , L b and L c are the first, second and third ligands of the complex, respectively; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; m+n+q equals the oxidation state of the metal M; and when m is greater than 1, multiple La are the same or different, and when n is 2, two L b are the same or different, and when q is 2, two L c are the same or different, L a , L b and L c may be linked to form a multidentate ligand; L b and L c is selected from the group consisting of the following structures, which may be the same or different at each occurrence: [ka] R a , R b and R c are the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 and CR C1 R C2 selected from the group consisting of X c and X d are O, S, Se, which may be the same or different for each occurrence. and NR N2 selected from the group consisting of R a , R b , R c , R N1 , R N2 , R C1 and R C2are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Said ligand L b , L c In the structure of a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring.
[0096] In this specification, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring means that adjacent substituent groups, for example, adjacent substituents R a adjacent substituents R b adjacent substituents R c adjacent substituents R aand R b adjacent substituents R a and R c adjacent substituents R b and R c adjacent substituents R a and R N1 adjacent substituents R b and R N1 adjacent substituents R a and R C1 adjacent substituents R a and R C2 adjacent substituents R b and R C1 adjacent substituents R b and R C2 adjacent substituents R a and R N2 adjacent substituents R b and R N2 each other and adjacent substituents R C1 and R C2 This means that any one or more of the adjacent substituents may be bonded to form a ring. Obviously, the adjacent substituents do not have to be bonded to form a ring.
[0097] According to one embodiment of the invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.
[0098] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.
[0099] According to one embodiment of the present invention, the metal M is Ir.
[0100] According to one embodiment of the present invention, L b is selected from the following structures, which may be the same or different at each occurrence: [ka] R1 to R7 each appearing may be the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. , a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
[0101] According to one embodiment of the present invention, L b is selected from the following structures, which may be the same or different at each occurrence: [ka] At least one of R1 to R3, at each occurrence, is the same or different and is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least one or two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.
[0102] According to one embodiment of the present invention, L b is selected from the following structures, which may be the same or different at each occurrence: [ka] At least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least one or two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.
[0103] According to one embodiment of the present invention, L b is selected from the following structures, which may be the same or different at each occurrence: [ka] At least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof, and / or at least two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.
[0104] According to one embodiment of the present invention, the metal complex has the formula Ir(L a ) m (L b ) 3-mand has a structure represented by formula 1-1 or 1-2, [ka] m is 1 or 2; X1~X2 are the same or different for each occurrence. x or N, and X3 to X7 are the same or different for each occurrence and are selected from CR i or N, and A1 to A4 are the same or different at each occurrence and are selected from CR ii or N, and X4 to X7 may be the same or different at each occurrence and are selected from CH, CR iii or N, and at least one of X4 to X7 is CR iii Selected from Y is SiR y R y , N.R. y , PR y , O, S or Se, and two R y When two R y are the same or different, R, R x , R y , R i , R iiR1, R2, R3, R4, R5, R6, and R7 each may be the same or different and each represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having 0 to 20 carbon atoms; R iiiare the same or different at each occurrence and each represents deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl group having 3 to 40 ring ... a substituted or unsubstituted C1-C20 heteroaryl group, a substituted or unsubstituted C3-C20 alkylsilyl group, a substituted or unsubstituted C6-C20 arylsilyl group, a substituted or unsubstituted C3-C20 alkylgermanium group, a substituted or unsubstituted C6-C20 arylgermanium group, a substituted or unsubstituted C0-C20 amino group, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R and R x , R y , R i , R ii and R iii may be bonded to form a ring, Adjacent substituents R1, R2, R3, R4, R5, R6, and R7 may be bonded to form a ring.
[0105] In this specification, "adjacent substituents R1, R2, R3, R4, R5, R6, and R7 may be bonded to form a ring" means that adjacent substituent groups, for example, adjacent substituents R1 and R2, adjacent substituents R1 and R3, adjacent substituents R1 and R7, adjacent substituents R2 and R3, adjacent substituents R2 and R7, adjacent substituents R3 and R7, adjacent substituents R4 and R5, adjacent substituents R4 and R6, adjacent substituents R4 and R7, adjacent substituents R5 and R6, adjacent substituents R5 and R7, and adjacent substituents R6 and R7, may be bonded to form a ring. Obviously, these substituents do not necessarily have to be bonded to form a ring.
[0106] According to one embodiment of the present invention, at least one or two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and / or at least one of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.
[0107] According to one embodiment of the present invention, at least two of R1 to R3, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof; and / or at least two of R4 to R6, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.
[0108] According to one embodiment of the present invention, the L b L b1 ~L b322 and L b1 ~L b322 The specific structure of is shown in claim 16, and c L c1 ~L c231 and L c1 ~L c231 The specific structure is shown in claim 16.
[0109] According to one embodiment of the present invention, the first metal complex is Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a )(L c )2,
[0110] The first metal complex is Ir(L a )2(L b ) structure, L a is the same or different for each occurrence of L a1 ~L a437 and L b L b1 ~L b322 and the first metal complex is Ir(L a )2(L c ) structure, L a may be the same or different for each occurrence of L a1 ~L a437 and L c L c1 ~L c231 and the first metal complex is Ir(L a )(L c )2 structure, L a L a1 ~L a437and L c is the same or different for each occurrence of L c1 ~L c231 Any one or any two selected from the group consisting of:
[0111] According to one embodiment of the present invention, the first metal complex is Ir(L a )2(L b ), Ir(L a )2(L c ) and Ir(L a )(L c )2,
[0112] The first metal complex is Ir(L a )2(L b ) structure, L a is the same or different for each occurrence of L a1 ~L a438 and L b L b1 ~L b322 and the first metal complex is Ir(L a )2(L c ) structure, L a may be the same or different for each occurrence of L a1 ~L a438 and L c L c1 ~L c231 and the first metal complex is Ir(L a )(L c )2 structure, L a L a1 ~L a438 and L c is the same or different for each occurrence of L c1 ~L c231 Any one or any two selected from the group consisting of:
[0113] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds RD-1 to RD-84, and specific structures of compounds RD-1 to RD-84 are shown in claim 17.
[0114] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds RD-1 to RD-88, the specific structures of compounds RD-1 to RD-84 are shown in claim 17, and the specific structures of compounds RD-85 to RD-88 are as follows: [ka]
[0115] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds RD-1 to RD-99, the specific structures of compounds RD-1 to RD-84 are set forth in claim 17, the specific structures of compounds RD-85 to RD-88 are set forth in the preceding examples, and the specific structures of compounds RD-89 to RD-99 are as follows: [ka] [ka]
[0116] According to one embodiment of the present invention, in Formula 2, at least one of W is CR W and wherein R W and each occurrence may be the same or different and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
[0117] According to one embodiment of the present invention, the first compound has a structure represented by any one of Formula 2-1, Formula 2-2, or Formula 3-1, [ka] W1 may be the same or different for each occurrence. w or selected from N, W2 may be the same or different for each occurrence. w or selected from N, L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 21 , Ar 22 , Ar 31 , Ar 32 , Ar 33 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R w are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents Rw may be bonded to form a ring.
[0118] According to one embodiment of the present invention, the first compound has a structure represented by any one of Formula 2-a to Formula 2-h and Formula 3-a, [ka] W1, W2, and W may be the same or different for each occurrence. w or selected from N, Ar 21 , Ar 22 , Ar 32 , Ar 33 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R ware the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R w may be bonded to form a ring.
[0119] In this specification, adjacent substituents R w may be bonded to form a ring means that any adjacent substituents R w It is clear that any adjacent substituents R w They do not necessarily have to be bonded to each other to form a ring.
[0120] According to one embodiment of the present invention, the first compound has a structure represented by any one of formulas 2-a to 2-c, 2-e, and 3-a.
[0121] According to one embodiment of the present invention, R ware the same or different at each occurrence and are selected from hydrogen, deuterium, halogen, cyano, hydroxyl, sulfanyl, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof.
[0122] According to one embodiment of the present invention, Ar 21 , Ar 22 has a structure represented by any one of formulas Ar-1 to Ar-4, which may be the same or different at each occurrence, and Ar 32 , Ar 33 each occurrence may be the same or different and have a structure represented by any one of formulas Ar-1 to Ar-6, [ka] Ar Q are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Q may be the same or different for each occurrence. Q or N, and Q1 is selected from O, S, Se, NR Q or CR Q R Q Q2 is selected from O, S or Se; R Qare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R Q may be bonded to form a ring.
[0123] In this specification, adjacent substituents R Q may be bonded to form a ring means that any adjacent substituents R Q It is clear that any adjacent substituents R Q They do not necessarily have to be bonded to each other to form a ring.
[0124] According to one embodiment of the present invention, the Q may be identical or different for each occurrence and may be C or CR. Q Q1 is selected from O, S or CR Q R Q Q2 is selected from O or S; R Qare the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.
[0125] According to one embodiment of the present invention, the Ar Q is selected from a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, and a phenanthrene group.
[0126] According to one embodiment of the present invention, the first compound is selected from the group consisting of Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-101, and Compounds 1-3-1 to 1-3-62, and specific structures of Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-101, and Compounds 1-3-1 to 1-3-62 are set forth in claim 21.
[0127] According to one embodiment of the present invention, hydrogen atoms in Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-101, and Compounds 1-3-1 to 1-3-62 may be partially or completely deuterated.
[0128] According to one embodiment of the present invention, the first compound is selected from the group consisting of Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-112, and Compounds 1-3-1 to 1-3-62. Specific structures of Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-101, and Compounds 1-3-1 to 1-3-62 are set forth in claim 21, and specific structures of Compounds 1-2-102 to 1-2-112 are as follows: [ka]
[0129] According to one embodiment of the present invention, hydrogen atoms in Compounds 1-1-1 to 1-1-104, Compounds 1-2-1 to 1-2-112, and Compounds 1-3-1 to 1-3-62 may be partially or completely deuterated.
[0130] According to one embodiment of the present invention, the second compound has a structure represented by formula 4-1: [ka] V1 to V6 are the same or different for each occurrence, and can be C, N, or CR. v and one of V1 to V6 is C and is attached to L3; L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 and Ar 42 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; R vare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R v may be bonded to form a ring.
[0131] In this specification, adjacent substituents R v may be bonded to form a ring means that any adjacent substituents R v It is clear that any adjacent substituents R v They do not necessarily have to be bonded to each other to form a ring.
[0132] According to one embodiment of the present invention, the second compound has a structure represented by formula 4-1-1 or 4-1-2, [ka] In formula 4-1-1, V1 to V5 may be the same or different and each occurrence may be C, N, or CR. vSelected from V 11 ~V 15 is N or CR, which may be the same or different for each occurrence. v1 and one of V1 to V5 is C and is bonded to L3; and in formula 4-1-2, V1 to V4 are the same or different and are C, N, or CR v Selected from V 11 ~V 14 is N or CR, which may be the same or different for each occurrence. v1 and one of V1 to V4 is C and is bonded to L3; and V is selected from O, S, or Se; L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 and Ar 42 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; R v , R v1are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R v , R v1 may be bonded to form a ring.
[0133] In this specification, adjacent substituents R v , R v1 may be bonded to form a ring means that adjacent substituent groups, for example, adjacent substituents R v adjacent substituents R v1 each other and adjacent substituents R v and R v1 This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of the substituents may be bonded to form a ring.
[0134] According to one embodiment of the present invention, in formula 4-1-2, V is selected from O or S.
[0135] According to one embodiment of the present invention, in formula 4-1-2, V is selected from O.
[0136] According to one embodiment of the present invention, V1 to V6 are C or CR, which may be the same or different for each occurrence. v Selected from V 11 ~V 15 may be the same or different for each occurrence. v1 Selected from.
[0137] According to one embodiment of the present invention, the R v , R v1 are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.
[0138] According to one embodiment of the present invention, at least one of V1 to V6 is CR v and wherein R v are the same or different at each occurrence and are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or V 11 ~V 15 At least one of the v1 and wherein R v , R v1 is the same or different at each occurrence and is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
[0139] According to one embodiment of the present invention, the R v , R v1 are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, and combinations thereof.
[0140] According to one embodiment of the present invention, the Ar 41 and Ar 42At least one of the groups has a two-fused ring or three-fused ring structure.
[0141] According to one embodiment of the present invention, the Ar 41 and Ar 42 and each occurrence may be the same or different and selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.
[0142] According to one embodiment of the present invention, the Ar 41 and Ar 42 are the same or different at each occurrence and are selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted indolocarbazole group, or a combination thereof.
[0143] According to one embodiment of the present invention, each occurrence of L1 to L3 may be the same or different and may be selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.
[0144] According to one embodiment of the present invention, each occurrence of L1 to L3 may be the same or different and selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
[0145] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds B-1 to B-228, and the specific structures of compounds B-1 to B-228 are shown in claim 27.
[0146] According to one embodiment of the present invention, the hydrogen atoms in the compounds B-1 to B-228 may be partially or completely deuterated.
[0147] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds B-1 to B-232, and the specific structures of compounds B-1 to B-228 are shown in claim 27, and the specific structures of compounds B-229 to B-232 are as follows: [ka]
[0148] According to one embodiment of the present invention, the hydrogen atoms in the compounds B-1 to B-232 may be partially or completely deuterated.
[0149] According to one embodiment of the present invention, the organic layer is an emitting layer, the first metal complex is an emitting material, the first compound is a host material, and the second compound is a host material.
[0150] According to one embodiment of the present invention, the first compound and the second compound are different.
[0151] According to one embodiment of the present invention, the electroluminescent element emits red, green or white light.
[0152] According to another embodiment of the present invention, there is further disclosed a display assembly including an electroluminescent device as described in the above embodiment.
[0153] According to another embodiment of the present invention, there is provided a compound composition comprising a first metal complex, a first compound, and a second compound, The first metal complex comprises a metal M and a ligand L coordinated with M. a wherein the metal M is selected from metals with a relative atomic mass greater than 40, and the L ahas a structure represented by formula 1, [ka] ring A, ring B, and ring C are each independently selected from a 5-membered unsaturated carbocyclic ring, an aryl ring having 6 to 30 carbon atoms, or a heteroaryl ring having 3 to 30 carbon atoms; R i , R ii , R iii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R iii , R x and R yare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R, R ii and R iii may be bonded to form a ring, The first compound has a structure represented by Formula 2 or Formula 3, [ka] W may be the same or different for each occurrence. w or N, and adjacent substituents R w may be bonded to form a ring, L, at each occurrence, may be the same or different and is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; R w are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; The second compound has a structure represented by formula 4: [ka] In formula 4, L1 to L3 each appearing are the same or different and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; Ar 41 ~Ar 43Further disclosed are compound compositions in which each occurrence is the same or different and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof.
[0154] Combination with other materials
[0155] The materials of the specific layers used in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132 to 0161 of U.S. Patent Application No. US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. The materials described or referenced are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.
[0156] The present specification describes that the materials of specific layers used in organic light-emitting devices can be used in combination with various other materials present in the device. Illustratively, the compounds disclosed herein can be used in combination with various emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. Combinations of these materials are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.
[0157] In the device examples, the device characteristics were also tested using equipment commonly used in the art (including, but not limited to, a deposition machine manufactured by Angstrom Engineering, an optical test system and a service life test system manufactured by Suzhou Fusida, an ellipsometer manufactured by Beijing Liangtang, etc.) in a manner familiar to those skilled in the art. Those skilled in the art will be familiar with the use of the above-mentioned equipment, test methods, and other related content, and will be able to reliably and unaffectedly obtain specific data for the sample, so the above-mentioned related content will not be repeated in this specification.
[0158] Example of the element
[0159] Element Example 1
[0160] First, a glass substrate (having a sheet resistance of 14 to 20 Ω / sq and a light-emitting area of 0.04 cm) with an indium tin oxide (ITO) anode of 120 nm in thickness was prepared. 2 After cleaning the substrate, it was treated with oxygen plasma and UV ozone. After the treatment, the substrate was dried in a glove box to remove moisture. The substrate was then attached to a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layer, a vacuum of approximately 10 -8For the TOF, the layers were deposited sequentially on the ITO anode by vacuum hot evaporation at a rate of 0.2 to 2 Å / s. Compounds HI and HT (weight ratio 3:97) were co-deposited to form a hole injection layer (HIL) with a thickness of 100 Å. Compound HT was used as a hole transport layer (HTL) with a thickness of 400 Å. Compound EB was used as an electron blocking layer (EBL) with a thickness of 50 Å. Compound RD-3, a dopant material, and compounds 1-2-2 and B-227 (weight ratio 3:38.8:58.2) were co-deposited to form an emitting layer (EML) with a thickness of 400 Å. Compound HB was used as a hole blocking layer (HBL) with a thickness of 50 Å. On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated to form an electron transport layer (ETL) with a thickness of 350 Å. Finally, a 1 nm thick Liq layer was evaporated to form an electron injection layer, and a 120 nm thick Al layer was evaporated to form a cathode. The device was then transferred to a glove box and encapsulated with a glass cover and an adsorbent to complete the device.
[0161] Element Example 2
[0162] The embodiment of Device Example 2 is similar to Device Example 1, except that Compound B-222 is used instead of Compound B-227 as the host material in the light-emitting layer.
[0163] Element Example 3
[0164] The embodiment of Device Example 3 is similar to Device Example 1, except that Compound 1-1-63 is used as the host material in the light-emitting layer instead of Compound 1-2-2.
[0165] Element Example 4
[0166] The embodiment of Device Example 4 is similar to Device Example 1, except that Compound RD-7 is used instead of Compound RD-3 as the dopant material in the light-emitting layer.
[0167] Element Example 5
[0168] The embodiment of Device Example 5 is similar to Device Example 4, except that Compound B-222 is used instead of Compound B-227 as the host material in the emissive layer.
[0169] Device Example 6
[0170] The embodiment of the device example 6 is similar to that of the device example 1, except that the compound RD-86 is used instead of the compound RD-3 as the dopant material in the light-emitting layer, and the doping weight ratio of the compound 1-2-2, the compound B-227 and the compound RD-86 in the light-emitting layer is adjusted to 38.8:59.2:2.
[0171] Device Example 7
[0172] The embodiment of Device Example 7 is similar to Device Example 6, except that Compound RD-88 is used instead of Compound RD-86 as the dopant material in the light-emitting layer.
[0173] Comparative Example 1 of the Element
[0174] The embodiment of Comparative Example 1 of the element is the same as that of Example 1 of the element, except that compound 1-2-2 is used as the host material in the light-emitting layer instead of compound 1-2-2 and compound B-227, and the doping weight ratio of compound 1-2-2 to compound RD-3 in the light-emitting layer is adjusted to 97:3.
[0175] Comparative example 2 of the element
[0176] The embodiment of Comparative Example 2 of the element is the same as that of Example 1 of the element, except that compound B-227 is used as the host material in the light-emitting layer instead of compound 1-2-2 and compound B-227, and the doping weight ratio of compound B-227 to compound RD-3 in the light-emitting layer is adjusted to 97:3.
[0177] Comparative Example 3 of the Element
[0178] The embodiment of Comparative Example 3 of the element is the same as that of Example 4 of the element, except that compound 1-2-2 is used as the host material in the light-emitting layer instead of compound 1-2-2 and compound B-227, and the doping weight ratio of compound 1-2-2 to compound RD-7 in the light-emitting layer is adjusted to 97:3.
[0179] Comparative Example 4 of the Element
[0180] The embodiment of Comparative Example 4 of the element is the same as that of Example 4 of the element, except that compound B-227 is used as the host material in the light-emitting layer instead of compound 1-2-2 and compound B-227, and the doping weight ratio of compound B-227 to compound RD-7 in the light-emitting layer is adjusted to 97:3.
[0181] Comparative Example 5 of the Element
[0182] The embodiment of Comparative Example 5 of the device is similar to Comparative Example 2 of the device, except that Compound RD is used instead of Compound RD-3 as the dopant material in the light-emitting layer.
[0183] Comparative Example 6 of the Element
[0184] The embodiment of Comparative Example 6 of the device is similar to that of Example 2 of the device, except that Compound RD is used instead of Compound RD-3 as the dopant material in the light-emitting layer.
[0185] Comparative Example 7 of the Element
[0186] The embodiment of Comparative Example 7 of the device is similar to Comparative Example 1 of the device, except that Compound RD is used instead of Compound RD-3 as the dopant material in the light-emitting layer.
[0187] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios given above.
[0188] [Table 1]
[0189] The structure of the material used in the element is as follows: [ka] [ka]
[0190] Table 2 shows the 15mA / cm 2 External quantum efficiency (EQE) data measured at a current density of 80 mA / cm 2 The data for service life (LT97) measured at a current density of 1000 kJ / s is shown.
[0191] [Table 2]
[0192] summary
[0193] From the data shown in Table 2, the following was found:
[0194] In the elements of Example 1, Comparative Example 1, and Comparative Example 2, the same first metal complex RD-3 selected by the present invention was used, while in Comparative Example 1, only the first compound 1-2-2 selected by the present invention was used as the sole host. Compared to Comparative Example 1, the EQE of Example 1 reached a maximum of 26.8%, the EQE was improved by 48.9%, and the service life was 77.4 hours, a 17-fold improvement in service life. In Comparative Example 2, only the second compound B-227 selected by the present invention was used as the sole host. Compared to Comparative Example 2, the EQE of Example 1 was improved by 44.1%, and the service life was improved by 8.1-fold. Compared to Comparative Example 2, the EQE of Example 3 reached a maximum of 24.3%, the EQE was improved by 30.6%, and the service life was 63.2 hours, a 6-fold improvement in service life. Examples 1 and 3 used first compounds with different skeletons selected by the present invention. The performance of the elements of Examples 1 and 3 was also excellent. These data demonstrate that the compound combination selected for this invention is one of the superior material combinations.
[0195] Comparing Example 2, Example 5, and Comparative Example 6, the device in Example 2 used the first metal complex RD-3 selected in the present invention, the device in Example 5 used the first metal complex RD-7 selected in the present invention, and the device in Comparative Example 6 used the luminescent material RD. Compared to Comparative Example 6, Example 2 had an EQE of up to 26.8%, an improvement of 54.9%, and a service life of 81.0 hours, a 26-fold improvement in service life. Example 5 had an EQE of up to 26.7%, an improvement of 54.3%, and a service life of 120.0 hours, a 39-fold improvement in service life. These data demonstrate that the combination of the first compound and second compound selected in the present invention with a different first metal complex selected in the present invention significantly improves the external quantum efficiency of the device while significantly improving the service life of the device compared to the combination of the first compound and second compound in the present invention with a metal complex not belonging to the present invention.
[0196] In Example 4 and Comparative Example 3, the same first metal complex RD-7 selected by the present invention was used in the device of Comparative Example 4, while in Comparative Example 3, only the first compound 1-2-2 selected by the present invention was used as the sole host. Compared to Comparative Example 3, the EQE of Example 4 reached a maximum of 26.5%, the EQE was improved by 30.5%, and the service life was 120 hours, a 13-fold improvement in service life. In Comparative Example 4, only the second compound B-227 selected by the present invention was used as the sole host. Compared to Comparative Example 4, the EQE of Example 4 reached a maximum of 26.5%, the EQE was improved by 36.6%, and the service life was 120 hours, a 14-fold improvement in service life. These data again demonstrate that the combination of the first compound selected by the present invention, the second compound, and the first metal complex selected by the present invention can significantly improve the external quantum efficiency of the device and significantly improve the service life of the device.
[0197] Comparative Examples 5 and 2 also use the second compound B-227 selected for the present invention, Comparative Example 2 uses the first metal complex RD-3 selected for the present invention, and Comparative Example 5 uses the luminescent material RD. Compared to Comparative Example 5, Comparative Example 2 uses a combination of the second compound and the first metal complex of the present invention, thereby achieving improved device performance. Compared to Comparative Example 2, Example 1 uses a combination of the first compound, second compound, and first metal complex selected for the present invention, thereby further improving the EQE and service life of Example 1 and achieving extremely excellent device performance. Similarly, Comparative Examples 7 and 1 also use the first compound selected for the present invention, Comparative Example 1 uses the first metal complex RD-3 selected for the present invention, and Comparative Example 7 uses the luminescent material RD. Compared to Comparative Example 7, Comparative Example 1 uses a combination of the first compound and the first metal complex selected for the present invention, thereby achieving improved device performance. Compared to Comparative Example 1, Example 1 uses a combination of the first compound, the second compound, and the first metal complex selected in the present invention, which further improves the EQE and service life of Example 1, making it possible to obtain extremely excellent device performance. These data again demonstrate that the compound combination selected in the present invention is an excellent material combination, and is capable of obtaining extremely excellent device performance.
[0198] Examples 6 and 7 demonstrate many different combinations of the first compound, second compound, and first metal complex of the present invention. Examples 6 and 7 achieve excellent device performance, with high efficiency and long service life, similar to other examples, even under conditions of a lower amount of emissive dopant (2%). Examples 6 and 7 achieve EQEs of up to 26.4% and 25.6%, respectively, significantly improved over the comparative example, with an improvement of at least 26%. At the same time, Examples 6 and 7 achieve service lives of up to 73 h and 62 h, respectively, improved by at least several times over the comparative example. Therefore, the combination of the first compound, second compound, and first metal complex selected for the present invention is demonstrated to be a material combination with excellent performance.
[0199] In summary, the combination of the first compound, the second compound, and the first metal complex selected in the present invention exhibits excellent device performance, can achieve higher external quantum efficiency, and can also significantly improve the device's service life. Therefore, it is demonstrated that the combination of the first compound, the second compound, and the first metal complex selected in the present invention has excellent application prospects.
[0200] It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Therefore, it will be apparent to those skilled in the art that the invention sought to be protected includes variations on the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.
Claims
1. An electronic component module including an electroluminescent element comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, The organic layer comprises a first metal complex, a first compound, and a second compound. The first metal complex comprises a metal M and a ligand L that coordinates with M. a The metal M is selected from metals with a relative atomic mass of 40 or more, and the L a It has the structure represented by formula 1, 【Chemistry 1】 Rings A, B, and C are each independently selected from a 5-membered unsaturated carbon ring, an aryl ring having 6 to 30 carbon atoms, or a heteroaryl ring having 3 to 30 carbon atoms. R i , R ii , R iii Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. Y is SiR y R y , GeR y R y , NR y , PR y , and is selected from O, S or Se, Two R's y If both exist at the same time, then two R y They may be the same or different. X 1 ~X 2 Each appearance is either the same or different CR x Or selected from N, R, R i , R ii , R iii , R x and R y Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted Alternatively, selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, Adjacent substituent R i , R x , R y , R, R ii and R iii They may be bonded together to form a ring. The first compound has a structure represented by formula 2 or formula 3, 【Chemistry 2】 W is the same or different each time it appears. w Or selected from N, adjacent substituent R w They may be bonded together to form a ring. L is selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof, with each occurrence being the same or different. Ar is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, with each occurrence being identical or different. R w Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted 2 carbon atoms. Selected from the group consisting of alkynyl groups of up to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, The second compound has a structure represented by formula 4, 【Transformation 3】 In formula 4, L 1 ~L 3 Each occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof. Ar 41 ~Ar 43 An electronic component module in which each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof, which may be identical or different each time they appear.
2. Said L a The electronic component module according to claim 1, wherein ring A and / or ring B are each independently selected from a five-membered unsaturated carbon ring, an aryl ring having 6 to 10 carbon atoms, or a heteroaryl ring having 3 to 10 carbon atoms, and ring C is selected from an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 6 to 10 ring atoms.
3. Said L a The structure is selected from one of the structures represented by formulas 1-a to 1-r. 【Chemistry 4】 In formulas 1-a to 1-r, X 1 ~X 2 Each appearance is either the same or different CR x Or selected from N, X 3 CR i Or selected from N, A 1 ~A 6 Each appearance is either the same or different CR ii Or selected from N, X 4 ~X 7 Each appearance is either the same or different CR iii or selected from N, and X 4 ~X 7 At least one of them is CR iii Selected from, Z is the same or different each time it appears. iv R iv , SiR iv R iv PR iv , O, S or NR iv Selected from, two R iv If both exist at the same time, then two R iv They are the same or different. Y is SiR y R y , NR y PR y , selected from O, S or Se, and two R y If both exist at the same time, then two R y They are the same or different. R, R x , R y , R i , R ii , R iii and R iv Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted Alternatively, selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, Adjacent substituent R i , R x , R y , R, R ii , R iii and R iv The electronic component module according to claim 1, wherein the components may be joined together to form a ring.
4. In Formula 1-a to Formula 1-r, X 1 ~X 2 are each independently selected from CR x ; X 3 is selected from CR i ; A 1 ~A 6 are each independently selected from CR ii ; X 4 ~X 7 are the same or different each time they appear and are selected from CR iii ; adjacent substituents R x , R i , R ii , R iii may combine to form a ring, the electronic component module according to claim 3.
5. R x , R i , R ii Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, and combinations thereof, and is the same or different each time it appears. R iii The electronic component module according to claim 3, wherein each occurrence is the same or different and is selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, and combinations thereof.
6. In Formulae 1-a to 1-r, A 1 ~A 4 Among them, at least one or two are CR ii Selected from, X 3 Is CR i Selected from, R i Each occurrence is selected from hydrogen, deuterium, halogens, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, or combinations thereof. R ii The electronic component module according to claim 3, wherein each occurrence is selected from deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, cyano groups, or combinations thereof.
7. The electronic component module according to claim 3, wherein R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C3-20 cycloalkyl group, substituted or unsubstituted C6-30 aryl group, substituted or unsubstituted C3-30 heteroaryl group, substituted or unsubstituted C3-20 alkylsilyl group, substituted or unsubstituted C6-20 arylsilyl group, or a combination thereof.
8. The electronic component module according to claim 3, wherein Y is selected from O or S in formulas 1-a to 1-r.
9. In formulas 1-a to 1-r, X 1 and X 2 Each of them is independently CR x Selected from, or X 1 CR x Selected from X 2 The electronic component module according to claim 3, wherein N is the same.
10. Ligand L a It has the structure represented by equation 5, 【Transformation 5】 In formula 5, Y is selected from O or S. R x1 , R x2 , R i , R ii1 , R ii2 , R ii3 , R ii4 , R, R iii1 , R iii2 , R iii3 , R iii4 Each occurrence is selected from the group consisting of hydrogen, deuterium, halogens, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, and combinations thereof. R iii1 , R iii2 , R iii3 , R iii4 The electronic component module according to claim 1 or 3, wherein at least one of the following is selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, substituted or unsubstituted C0-C20 amino groups, and combinations thereof, with each occurrence being the same or different.
11. At least one or two of R x1, R x2, R iii1, R iii2, R iii3, R iii4, and / or R iii1, R iii2, R iii3, R iii4 The electronic component module according to claim 10, wherein at least one or two of the following are selected, identical or different each time they appear: deuterium, halogen, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 ring cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, substituted or unsubstituted C3-C20 alkylsilyl group, substituted or unsubstituted C6-C20 arylsilyl group, or a combination thereof, and R is selected from halogen, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 ring cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, substituted or unsubstituted C3-C20 alkylsilyl group, substituted or unsubstituted C6-C20 arylsilyl group, or a combination thereof.
12. R iii1 , R iii2 , R iii3 , R iii4 At least one or two of the following, and R ii1 , R ii2 , R ii3 , R ii4 At least one or two of the following are selected from the group consisting of deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, or combinations thereof, wherein R is selected from halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alkylsilyl groups, substituted or unsubstituted C6-C20 arylsilyl groups, or combinations thereof, as described in claim 10.
13. L a Each occurrence is selected from a group consisting of the following structures, which may be identical or different: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 Said L a1 ~L a437 The electronic component module according to claim 1, wherein the hydrogen in the structure may be partially or entirely deuterated.
14. The first metal complex is M(L a ) m (L b ) n (L c ) q Having a structure, Metal M is selected from metals with a relative atomic mass greater than 40, L a , L b and L c These are the first, second, and third ligands of the complex, respectively, m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m + n + q is equal to the oxidation state of the metal M, and if m is greater than 1, there are multiple L a They are the same or different, and if n is 2, then there are two L b They are the same or different, and if q is 2, then there are two L c They are the same or different. L a , L b and L c These may be bound together to form a polydentate ligand. L b and L c Each occurrence is selected from a group consisting of the following structures, which may be identical or different: 【Chemistry 28】 R a , R b and R c Each occurrence of this symbol represents a single substitution, multiple substitutions, or no substitution, whether identical or different. X b Each occurrence is either the same or different as O, S, Se, NR N1 and CR C1 R C2 Selected from the group consisting of, X c and X d Each occurrence is either the same or different, O, S, Se, and NR N2 Selected from the group consisting of, R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and Selected from the group consisting of substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 The electronic component module according to claim 1 or 13, wherein the components may be joined together to form a ring.
15. The electronic component module according to claim 14, wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au, or Cu.
16. L b The electronic component module according to claim 14, wherein each occurrence is selected from the following structures, either identical or different. 【Chemistry 29】 (R 1 ~R 7 Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted Alternatively, it may be selected from the group consisting of unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
17. L b Each occurrence may be the same or different 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 Selected from the group consisting of, L c Each occurrence may be the same or different 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 An electronic component module according to claim 14, selected from the group consisting of the following.
18. The first metal complex is Ir(L a ) 2 (L b ), Ir(L a ) 2 (L c ) and Ir(L a ) (L c ) 2 Having a structure represented by any one of the following, The first metal complex is Ir(L a ) 2 (L b ) has the structure L a Each occurrence is either the same or different L a1 ~L a437 One or two types selected from the group consisting of L b is, L b1 ~L b322 It is one selected from the group consisting of the above, and the first metal complex is Ir(L a ) 2 (L c ) has the structure L a Each appearance is either the same or different L a1 ~L a437 One or two types selected from the group consisting of L c is, L c1 ~L c231 It is one selected from the group consisting of the above, and the first metal complex is Ir(L a ) (L c ) 2 Having the structure L a is, L a1 ~L a437 It is one of the groups consisting of L c Each occurrence is either the same or different L c1 ~L c231 The electronic component module according to claim 17, which is one or two selected from the group consisting of the following.
19. The electronic component module according to claim 18, wherein the first metal complex is selected from the group consisting of compounds RD-1 to RD-84. 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】
20. The electronic component module according to claim 1, wherein the first compound has a structure represented by any one of formulas 2-1, 2-2, or 3-1. 【Chemistry 57】 (W 1 Each appearance is either the same or different CR w Or selected from N, W 2 Each appearance is either the same or different C, CR w Or selected from N, L is selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof, with each occurrence being the same or different. Ar 21 Ar 22 Ar 31 Ar 32 Ar 33 Each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, which may be the same or different each time they appear. R w Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted 2 carbon atoms. Selected from the group consisting of alkynyl groups of up to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, Adjacent substituent R w (They may be joined together to form a ring.)
21. The first compound has a structure represented by any one of formulas 2-a to 2-h and formula 3-a, 【Transformation 58】 W 1 , W 2 , W is the same or different each time it appears CR w Or selected from N, Ar 21 Ar 22 Ar 32 Ar 33 Each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, which may be the same or different each time they appear. L is selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof, with each occurrence being the same or different. R w Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, or substituted or unsubstituted 2 carbon atoms. Selected from the group consisting of alkynyl groups of up to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, Adjacent substituent R w The electronic component module according to claim 1 or 20, wherein the components may be joined together to form a ring.
22. The electronic component module according to claim 21, wherein the first compound has a structure represented by any one of formulas 2-a to 2-c, 2-e, and 3-a.
23. The electronic component module according to claim 21, wherein R w is selected from hydrogen, deuterium, halogen, cyano group, hydroxyl group, sulfanyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, or a combination thereof, with each occurrence being the same or different.
24. Ar 21 Ar 22 Each instance of Ar has a structure that is identical or different and can be represented by one of the formulas Ar-1 to Ar-4, 32 Ar 33 Each instance has a structure that is identical or different and can be represented by one of the formulas Ar-1 to Ar-6. 【Chemistry 59】 Ar Q Each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, which may be the same or different each time they appear. Q is the same or different each time it appears, C, CR Q Or selected from N, Q 1 O, S, Se, NR Q or CR Q R Q Selected from, Q 2 is selected from O, S, or Se, R Q Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted carbon atoms Selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Adjacent substituent R Q The electronic component module according to claim 21, wherein the components may be joined together to form a ring.
25. Q is selected from C or CR Q, which may be the same or different each time it appears; Q1 is selected from O, S or CR Q R Q; Q2 is selected from O or S; R Q is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and combinations thereof, which may be the same or different each time it appears. The electronic component module according to claim 24, wherein Ar Q is selected from a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, or a phenanthrene group.
26. The first compound is selected from the group consisting of the following compounds: 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical Formula 77】 【Transformation 78】 【Chemistry 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 The electronic component module according to claim 1, wherein the hydrogen in compounds 1-1-1 to 1-1-104, compounds 1-2-1 to 1-2-101, and compounds 1-3-1 to 1-3-62 may be partially or entirely deuterated.
27. The second compound has the structure represented by formula 4-1, 【Chemistry 83】 V 1 ~V 6 Each occurrence is either the same or different C, N, or CR. v Selected from and V 1 ~V 6 One of them is C and L 3 Combine, L 1 ~L 3 Each occurrence is selected from the same or different single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof. Ar 41 and Ar 42 Each occurrence is selected from identical or different substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof. R v Each occurrence may be the same or different hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted Alternatively, selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, Adjacent substituent R v The electronic component module according to claim 1, wherein the components may be joined together to form a ring.
28. The second compound has a structure represented by formula 4-1-1 or formula 4-1-2, 【Chemical 84】 In formula 4-1-1, V1 to V5 are selected from C, N, or CR v, either identically or differently each time they appear, V11 to V15 are selected from N or CR v1, either identically or differently each time they appear, and one of V1 to V5 is C and is bound to L3, In formula 4-1-2, V1 to V4 are selected from C, N, or CR v, either identically or differently each time they appear, V11 to V14 are selected from N or CR v1, either identically or differently each time they appear, and one of V1 to V4 is C and is bound to L3, V is selected from O, S, or Se. L1 to L3 are selected from the same or different single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, or combinations thereof, each time they appear. Ar 41 and Ar 42 are selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof, each time they appear, and either identically or differently. R v, R v1 are the same or different each time they appear, and are hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted Alternatively, selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof, The electronic component module according to claim 27, wherein adjacent substituents R v and R v1 may be bonded together to form a ring.
29. The electronic component module according to claim 27, wherein V is selected from O or S in formula 4-1-2.
30. V 1 ~V 6 Each occurrence is either the same or different C or CR v Selected from, V 11 ~V 15 Each appearance is either the same or different CR v1 An electronic component module according to claim 27, selected from among.
31. The electronic component module according to claim 30, wherein at least one of V1 to V6 is selected from CRv, and Rv is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, with the same or different substituted groups appearing each time, or at least one of V11 to V15 is selected from CRv1, and Rv1 is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, with the same or different substituted groups appearing each time.
32. Ar 41 and Ar 42 The electronic component module according to claim 27, wherein each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, or a combination thereof, which may be the same or different each time they appear.
33. The electronic component module according to claim 32, wherein Ar 41 and Ar 42 are selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted indolocarbazole group, or a combination thereof, with each occurrence being the same or different.
34. L 1 ~L 3 The electronic component module according to claim 1 or 27, wherein each occurrence is selected from single-bonded, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
35. The electronic component module according to claim 34, wherein L1 to L3 are selected from single bonds, substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, substituted or unsubstituted biphenylene groups, or combinations thereof, with each occurrence being the same or different.
36. The second compound is selected from the group consisting of the following compounds: 【Chemical 85】 【Chemical 86】 【Chemistry 87】 【Chemical 88】 【Chemistry 89】 【Chemistry 90】 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 【Chemical 95】 【Chemistry 96】 【Chemistry 97】 【Chem.98】 【Chem.99】 【Chemistry 100】 【Chemistry 101】 【Chemical Engineering 102】 【Chemistry 103】 【Chemical 104】 【Chemistry 105】 【Chemistry 106】 The electronic component module according to claim 1, wherein the hydrogen in compounds B-1 to B-228 may be partially or entirely deuterated.
37. The electronic component module according to claim 1, wherein the organic layer is a light-emitting layer, the first metal complex is a light-emitting material, the first compound is a host material, and the second compound is a host material.
38. The electronic component module according to claim 1, wherein the electroluminescent element emits red light, green light, or white light.
39. A consumer product comprising the electronic component module described in claim 1.